Sodium borohydride → HCID 59759989, Verbindung

HRID 1010699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010699
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C:9]=1[C:21]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[O:22].[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C:9]=1[CH:21]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[OH:22]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 67313482HCID 67313482, Verbindung

Produkt 1

HCID 59759989HCID 59759989, VerbindungAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 80 mg (0.19 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)carbonyl]isoxazole in 3 mL of ethanol at 0° C. was added 40 mg (1.06 mmol) of sodium borohydride. The mixture was stirred for 2 hrs and then diluted with ethyl acetate. The ethyl acetate solution was washed with saturated sodium chloride solution and dried over magnesium sulfate. The drying agent was filtered off, and the ethyl acetate was removed by rotoevaporation. The crude product was purified by prep TLC to give 65 mg (0.15 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]-isoxazole. 1H NMR (CDCl3): δ 5.80 (br s, 1), 6.97 (m, 1), 8.23 (br s, 1), and 8.28 ppm (br s, 1). MS m/z: 431.0 (M+H).

Aufarbeitung

  1. washThe ethyl acetate solution was washed with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. customthe ethyl acetate was removed by rotoevaporation
  5. customThe crude product was purified by prep TLC

Quellen und Nachweise

ORD-Eintrag
ord-ead0f3392afc413ca94ac346ad943598
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977341B2

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